


Silk

by brorotica



Category: Supernatural
Genre: Anal Play, Anal Sex, M/M, Sexual Content, Teenagers, Underage Sex
Language: English
Status: Completed
Published: 2012-08-20
Updated: 2012-08-20
Packaged: 2017-11-12 12:23:23
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,539
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/490962
Author URL: https://archiveofourown.org/users/brorotica/pseuds/brorotica
Summary: <blockquote class="userstuff">
              <p>Dean Winchester is seventeen when he steals a pair of Jo’s panties.</p>
            </blockquote>





	Silk

**Author's Note:**

> Anal sex. Making out, some strong language. Dean is in girl's underwear throughout. Both boys are seventeen.

Dean Winchester is seventeen when he steals a pair of Jo’s panties.

He doesn’t take them out of any curiosity about her vagina- she’s like a sister, for god’s sake- but because they’re black as pitch, covered in tiny little lightning bolts, and look like they might fit him, too. They’re hanging off her clean laundry basket, waiting to be put back in the drawer, and he decides, on a whim, that he’ll take them. Surreptitiously, he slips them in his pocket and doesn’t take them out until he gets home.

When he finally works up the courage to pull them on, it's after midnight, and he can hear his father asleep in the room across the hall, his brother still downstairs, watching some show on TV. Dean takes a deep breath, tugs off his boxers, and replaces them with the panties. They're snug but comfortable, black cotton clinging to his cock and the slight frills around the waist- little loops and turns he didn't notice before- exacerbating his already toned hips.

Dean runs his fingers along the fabric and smiles at himself in the mirror. He likes them, truthfully. They fit so well, like he thought they would, and he likes the stark contrast of his flat chest against the womanly curve of his waist, the slightly bowed legs, the smooth skin of his thighs. Some part of him feels as though this is wrong- after all, he took the panties- but the wrongness is outweighed by the fact that for the first time, he's genuinely comfortable looking at himself. He wonders how odd it would look if he bought some of his own.

He does, no matter what the consequences might be. Takes fifty dollars and his dad's car and drives into town, stops by Victoria's secret and buys a few pairs, all satiny pink and lacy black and a deep sky blue that matches his boyfriend's eyes. He wears them under his jeans, careful that the tops don't peek out if he bends down, that the only person who gets to see him with them on is himself, in the mirror, at night. All smooth legs- he's taken up shaving- and curved ass, a chick from the waist down. He likes it, likes how it looks and how he feels and how his chest bubbles up with happiness when he catches a glimpse of the lace during the day.

Castiel comes over to study one night and Dean is wearing the blue pair, the boy shorts, the ones rimmed with lace and topped with a bow. They fit against his cock as snug as anything, as perfect as anything, and he's wholly himself. If Castiel notices how happy he is, he doesn't say anything. They're splayed out on his bed, Castiel reading Hamlet out loud in the serious voice he adopts for class projects, Dean staring at the ceiling and fiddling with a loop on his jeans. Castiel suddenly stops reading. "What are those?" he asks, and Dean glances down to find that maybe fiddling wasn't the best idea.

The blue panties are peeking from above his waist and Dean almost blushes- almost- before frowning and hiking his pants up. "Underwear."

"Girl's?" Castiel says, but he doesn't sound scandalized. Dean shoots him an uncertain look and Castiel is smiling at him, at least as much as he ever does. "I want to see. Can I?"

Dean swallows because holy shit, he's kissed Cas before but this is a Big Fucking Deal. He nods, though, sitting up and getting onto his knees, undoing his jeans and pushing them down slowly. He's a little frightened of what Castiel might think, but the expression on the other teenager's face is solemn interest, not anything ridiculing or upset.

Dean gets his jeans down to his knees and Castiel reaches out, looking at Dean with the utmost curiosity before running a finger along the hem of the panties. Dean lets out a breath he didn't realize he was holding and Castiel smiles, moving forward on the bed and pushing up Dean's shirt, planting a line of kisses on Dean's hips, moving from one side to the other, tongue trailing the line of the underwear.

Dean relaxes entirely and fists a hand in Castiel's hair, looking down at him. "I thought of you when I bought them," he says softly. "At least this pair."

"There's more?" Castiel asks, and there's a hint of amusement in his voice as he tilts his head up, resting his chin against Dean's stomach. "Why?"

"I like them," Dean says, and it's a little unsure. "I just... they make me feel good. Inside."

Castiel nods and doesn't ask any more questions other than, "Do you want to have sex?"

Dean grins and lets his hand fall from Castiel's hair, tracing the line of his jaw, his neck, his shoulder. "Sure," he says, and Castiel grins, pushing him back on the bed. Dean lets Castiel pin him down, lets Castiel kiss him, all teeth and tongue and mouth. It's hot and much-needed, more than sexually, because Castiel knows and Castiel doesn't care. Castiel doesn't mind it in the slightest.

Castiel runs his tongue along Dean's lower lip, nuzzling into him, his hands running down Dean's chest, along his sides. He finally stops at his hips, fingers dipping into the panties slightly before pulling them out again. He breaks the kiss and Dean keens somewhere deep in his throat, eyes flickering over Castiel's face before the other man murmurs, "Can I fuck you with them on?"

"You can do whatever," Dean says, but his cheeks turn red nonetheless and he feels a little overwhelmed. It's a good overwhelmed, though, an overwhelmed where he's wanted this for so long and so badly that he isn't sure what he's supposed to do now that he has it laying on top of him. Castiel's denim-clad cock rubs against Dean's ass, and silk isn't enough to stop the pleasure, isn't enough to keep Dean from groaning, his eyes flickering shut. "Fuck, Cas."

Castiel laughs, a rare sound on its own, and drops down, teeth grazing along Dean's neck, biting at his chest. His tongue circles around one of Dean's nipples, sensitive and hard, but before Dean can get any real pleasure from it, Castiel's moving on again. He slides down his body, tongue teasing at spots Dean didn't even know were sensitive. He reaches the front of the panties and hesitates, Dean panting in anticipation before Castiel's lips press a small string of kisses along his bulging cock, which is already leaving a stain of precome on the panties. Castiel brings Dean to full arousal, his dick tenting against the silk underwear, and there's a beat where Castiel doesn't do anything, where he doesn't touch him. Dean glances down and Castiel is shimmying out of his own jeans, palming at his own cock through his boxers, and he grins almost wickedly before Castiel leans over him, tugging open the drawer of the stand beside the bed.

He tugs out the lube that, until now, was used only for masturbation, and there's a split second where neither of them can find a condom, Dean finally producing one from his wallet. "These are prone to burst," Castiel says, and Dean shoves his hips up impatiently.

"I'm not getting pregnant so just fuck me."

Castiel hastily rolls the condom down over his cock and coats his fingers with lube, pulling the panties to one side and pressing two fingers into Dean. Dean hisses, the intrusion not unwelcome, and he tilts his head back as Castiel scissors, spreading him open far more than Dean's ever dared to himself. "Please," he finally whimpers, unable to bear the teasing. "Please, Cas."

Castiel obliges willingly, slathering his condom-covered dick with the lubricant and spreading Dean's legs. He pushes into him and Dean bites back a cry, knowing that his dad might hear if he doesn't. He doesn't want to risk it. Castiel buries himself inside Dean entirely, and he's thick and warm and all-encompassing. Dean is beginning to think his mind is going to burst from the feeling until Castiel pulls out a little clumsily, cock slipping from Dean's ass. "Fuck," Castiel murmurs, and Dean almost laughs before Castiel slams into him again, hitting the bundle of nerves and forcing Dean to arch off the bed.

Castiel manages to strike up a rhythm, however unsure he is, and Dean is soon grabbing at the sheets, fingers digging into the mattress, eyes squeezed closed. "M'gonna come," he whimpers, totally undone, and Castiel slams into him one more time. Dean comes, seed spilling all over the blue panties. They're probably wrecked now, but Dean doesn't give a shit.

A few minutes later and Castiel finishes up, pulling out of Dean and pulling the condom off slowly, tying a knot in it and tossing it in the trash beside Dean's desk. They stare at each other for a few moments before Dean can't help but laugh, leaning up in order to swat at Castiel's arm. "Why are you looking at me like that?"

"You should get a crotchless pair," Castiel says, laying down beside him, and Dean grins.

It's a pretty great idea.


End file.
